During that stretch, Johnny Carson’s eventual successor became the symbol of the company man. He was also the punching bag for just about every late-night host on TV at the time. Jimmy Kimmel famously dressed up as Jay and later agreed to appear on Leno’s show, only to spend the interview taking shots at the whole Tonight Show shake-up.

David Letterman has sharply criticized CBS, calling executives “lying weasels” for claiming Stephen Colbert’s Late Show cancellation was purely financial. Letterman alleges the move was tied to Paramount Global’s $8 billion merger with Skydance ...

A resurfaced video from Late Night with David Letterman shows the talk show host and his comedian guest playing a Kentucky Derby name game.

Is retirement really the dream it’s made out to be? David Letterman challenges the idea, and experts weigh in on purpose, fulfillment and life after work.

The pop-culture pros at Cracked uncover the story of a late night legend who made life very difficult for the actor cast to portray him on screen.